Tetrahedron Letters Vol. 53, Issue 47, 2012 Contents COMMUNICATIONS An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl 4 pp 6321–6325 Gourhari Maiti*, Utpal Kayal, Rajiv Karmakar, Rudraksha N. Bhattacharya O HAuCl 4 (5 mol%) DCM, H 2 O, rt, 24 h OH O R R R 1 R 1 Yield 52-87% Ruthenium- and lipase-catalyzed inversion of L-lactates pp 6326–6328 Ivan A. Shuklov*, Natalia V. Dubrovina, Joachim Schulze, Wolfgang Tietz, Klaus Kühlein, Armin Börner* OR OH O OR OAc O Ru-cat, enzyme, acylating agent up to 99 %ee Acantholactone, a new manzamine related alkaloid with an unprecedented d-lactone and e-lactam ring system pp 6329–6331 Amir E. Wahba, Yann Fromentin, Yike Zou, Mark T. Hamann* O N N H N N H OH O O (12S) (24R) (25R) (26R) Acantholactone 20 28 33 14 17 22 34 36 35 6311 Contents lists available at SciVerse ScienceDirect Tetrahedron Letters journal homepage: www.elsevier.com/locate/tetlet
Transcript
Tetrahedron Letters Vol. 53, Issue 47, 2012
Contents
COMMUNICATIONS
An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysisof HAuCl4
pp 6321–6325
Gourhari Maiti*, Utpal Kayal, Rajiv Karmakar, Rudraksha N. Bhattacharya
OHAuCl4 (5 mol%)
DCM, H2O, rt, 24 h OH
O
RR
R1R1
Yield 52-87%
Ruthenium- and lipase-catalyzed inversion of LL-lactates pp 6326–6328
Ivan A. Shuklov*, Natalia V. Dubrovina, Joachim Schulze, Wolfgang Tietz, Klaus Kühlein, Armin Börner*
OROH
O
OROAc
O
Ru-cat, enzyme,acylating agent
up to 99 %ee
Acantholactone, a new manzamine related alkaloid with an unprecedented d-lactone and e-lactam ring system pp 6329–6331
Amir E. Wahba, Yann Fromentin, Yike Zou, Mark T. Hamann*
O
NNH
N
N
HOH
O
O (12S )
(24R)
(25R) (26R)
Acantholactone
20
2833
1417
22 34
36
35
6311
Contents lists available at SciVerse ScienceDirect
Tetrahedron Letters
journal homepage: www.elsevier .com/ locate/ tet le t
Concise synthesis of N3- and N6-monoprotected 3,6-diazabicyclo[3.1.1]heptanes; useful intermediates for thepreparation of novel bridged bicyclic piperazines
pp 6332–6334
Daniel P. Walker*, Matthew W. Bedore
Cl
O O
Cl NN
NsBOC
HNN
BOC
NNH
Ns
2d
2e
6-steps
2f
1-step
Functionalization of BINOL and application in the homo- and heterogeneous enantioselective epoxidation ofa,b-unsaturated ketones
pp 6335–6338
Moulay Youness El Kadiri, Eric Framery, Bruno Andrioletti*
R Ph
O
R Ph
OOLn/L
OxOH
OH
N
Z
L =
Z = H or C C-CH2-N(CH3)2
Novel sesquiterpene lactones from Eremanthus seidelii pp 6339–6342
João Paulo Barreto Sousa, José Carlos Tomaz, Cecilia C. P. da Silva, Javier Ellena, Norberto Peporine Lopes,João Luis Callegari Lopes*
Synthesis of isomeric corniculatolides pp 6343–6346
Gajanan N. Raut, Kasturi Chakraborty, Priyanka Verma, Rajesh S. Gokhale, D. Srinivasa Reddy*
Stereospecific synthesis of C-arabinofuranosides and carba-disaccharide analogues of Motif C of cell wall AGcomplex of Mtb
pp 6347–6350
Rahul S. Patil, Ketan M. Ahire, C. V. Ramana*
MeO
R
O
HO
OH
R =
ROO O
OMs
OMe
OMeH+
Furan RingTransposition
i. H+
ii. NaBH4
HO
R
O
HO
OH
OMsO
O O
OMeOMsO
OO
MeO i. H+, ii. H+
iii. NaBH4
O
HO
OHHO
O
HO
OH
OH
Double Furan RingTransposition
Spiroazetidine–piperidine bromoindane as a key modular template to access a variety of compounds via C–C andC–N bond-forming reactions
pp 6351–6354
Dilinie P. Fernando, Wenhua Jiao, Jana Polivkova, Jun Xiao, Steven B. Coffey, Colin Rose, Allyn Londregan, James Saenz,Ramsay Beveridge, Yingxin Zhang, Gregory E. Storer, Derek Vrieze, Noe Erasga, Ryan Jones, Vishal Khot, Kimberly O. Cameron,Kim F. McClure, Samit K. Bhattacharya, Suvi T. M. Orr*
N
N
Boc
Br
N
N
Boc
R
N
N
Boc
Ar
(pinB)2Ar-X, [Pd]
NH-hetero-cycles, [M]
XCO2H, [M]
R = N-linked heterocycles,-CO2H
Ar = C-linked aryl,heteroaryl
one-pot
Direct b-amination reaction in porphyrin systems—a simple route to compounds containing two nitrogensubstituents at both b-positions of the same pyrrole unit
One-pot synthesis of meso–meso directly linked diheteroporphyrin dimers pp 6376–6379
Yi-Zhou Zhu, Yan Zhu, Shao-Chun Zhang, Hai-Bin Song, Jian-Yu Zheng*
A one-pot synthesis strategy to synthesize the novel meso–meso directly linked dithiaporphyrin dimer (DDSP) was achieved for the first time. And thedescribed methodology also can work smoothly to prepare the oxathiaporphyrin dimers DOSP and DSOP. This work offers a facile and convenient way toget the meso–meso directly linked diheteroporphyrin dimer from simple non-porphyrin precursors.
Teresa A. F. Cardote, Joana F. B. Barata*, M. Amparo F. Faustino*, Annegret Preuß, M. Graça P. M. S. Neves, José A. S. Cavaleiro,Catarina I. V. Ramos, M. Graça O. Santana-Marques, Beate Röder
NH HN
NNH
F
F
FF
F
F
F F
F
F
F F
FF
O
O
O
O OO
O
OO
OO
ONH HN
NNH
F
F
FF
F
F
F
F F
F
F F
FF
Highly-substituted pyrazoles and pyridazines by MIRC reactions of hydrazone anions and nitrobutadienic fragments pp 6394–6400
Lara Bianchi, Alessandro Carloni-Garaventa, Massimo Maccagno, Giovanni Petrillo, Carlo Scapolla, Cinzia Tavani*
An efficient and convenient method for synthesizing new derivatives of pyrido[2,3-e]pyrrolo[1,2-a][1,4]diazepine-5,10-dione via Sonogashira, Suzuki–Miyaura, and Stille cross-coupling reactions
pp 6401–6405
Abderrahman El Bouakher, Gildas Prié, Mina Aadil, Said Lazar, Ahmed El Hakmaoui, Mohamed Akssira*,Marie-Claude Viaud-Massuard*
N
CO2H
NH2 N NH
N
O
O
R
Palladium-catalyzed double N-arylation to synthesize multisubstituted dibenzoazepine derivatives pp 6406–6408
Xiaoyun Zhang, Yuan Yang, Yun Liang*
NR
+ R NH2Pd2dba3, DPEphos
Cs2CO3, Toluene120 oC
R2R1
Br Br
R1 R2
Improved recognition of alkylammonium salts by ion pair recognition based on a novel heteroditopicpillar[5]arene receptor
pp 6409–6413
Mengfei Ni, Yangfan Guan, Lin Wu, Chao Deng, Xiaoyu Hu, Juli Jiang, Chen Lin*, Leyong Wang
Slipping synthesis of cucurbit[7]uril-based [2]rotaxane in organic environment pp 6414–6417
Microwave-assisted synthesis of novel oligomeric rod-disc hybrids pp 6446–6450
Shilpa Setia, Sumyra Sidiq, Santanu Kumar Pal*
O
O
OO
OO
O
OO
O
NC O(CH2)n
Microwave-assisted green syntheses of five new oligomeric liquid crystals (LC) are reported consisting of rufigallol-based core attached to which8-cyanobiphenyl units via flexible alkyl spacers.
Efficient synthesis and reaction pathway studies of novel fused morpholine oxadiazolines for use as gammasecretase modulators
pp 6451–6455
Xianhai Huang*, Dmitri Pissarnitski, Hongmei Li, Theodros Asberom, Hubert Josien, Xiaohong Zhu, Monica Vicarel,Zhiqiang Zhao, Murali Rajagopalan, Anandan Palani, Robert Aslanian, Zhaoning Zhu, William Greenlee, Alexei Buevich
O
F
FEtO
PEtO
O
Br
N OH+
N
N OO
OH
Aβ42 IC50 = 16 nM
F
F
NN
MeO
ON
Facile C–C bond cleavage of b-diketones by tin(IV) porphyrin complex pp 6456–6459
Atul Pratap Singh, Bu Bae Park, Hee-Joon Kim*
Microwave-assisted efficient synthesis of spiroquinoline derivatives via a catalyst- and solvent-free aza-Diels–Alderreaction
*Corresponding authorSupplementary data available via SciVerse ScienceDirect
COVER
A one-pot synthesis of micron-sized and nanoscale poly(N-acryloxysuccinimide-co-N-vinylpyrrolidone) particlesTetrahedron Letters 2012, 53, 6436–6438.Published by Elsevier Ltd.
Abstracted/indexed in: AGRICOLA, Beilstein, BIOSIS Previews, CAB Abstracts, Chemical Abstracts, Chemical Engineering andBiotechnology Abstracts, Current Biotechnology Abstracts, Current Contents: Life Sciences, Current Contents: Physical,Chemical and Earth Sciences, Current Contents Search, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, Medline,PASCAL, Research Alert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus�.Full text available on SciVerse ScienceDirect�
